Journal
CHEMICAL COMMUNICATIONS
Volume 50, Issue 53, Pages 6973-6976Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c4cc02279c
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- DST India
- CSIR India
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Cascade reactions of 1,3-dicarbonyls with Morita-Baylis-Hillman acetates of nitroalkenes using a quinine derived chiral squaramide organocatalyst led to the formation of pyranones and pyranonaphthoquinones in good to excellent yields and high diastereo-and enantioselectivities. Representative examples of the reaction scale-up with a much lower catalyst loading without an appreciable loss of selectivities and synthetic transformations of the products are also reported here. The compounds described herein for the first time were evaluated against the infective bloodstream form of Trypanosoma cruzi, the etiological agent of Chagas disease, since the structures are related to bioactive alpha-lapachones.
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